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Synthesis of Functionalized Tetrahydrobenzofuran via Cascade Cycloaddition Involving Silyloxyallyl Cation Intermediate

Abstract

An expedient synthesis of highly substituted tetrahydrobenzofuran via unsymmetrical silyloxyallyl cation is reported. Conveniently generated under catalytic Brønsted acid conditions, nucleophilic capture of this reactive intermediate with silylenolate, followed by cascade Paal-Knorr cyclization in the presence of tosic acid monohydrate effectively constructed the tetrahydrobenzofuran core in a single synthetic step operation.

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Article information


Accepted
24 Mar 2020
First published
26 Mar 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Synthesis of Functionalized Tetrahydrobenzofuran via Cascade Cycloaddition Involving Silyloxyallyl Cation Intermediate

F. Badmus, J. Malone, F. R. Fronczek and R. Kartika, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/D0CC01796E

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